JP2018052972A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2018052972A5 JP2018052972A5 JP2017234081A JP2017234081A JP2018052972A5 JP 2018052972 A5 JP2018052972 A5 JP 2018052972A5 JP 2017234081 A JP2017234081 A JP 2017234081A JP 2017234081 A JP2017234081 A JP 2017234081A JP 2018052972 A5 JP2018052972 A5 JP 2018052972A5
- Authority
- JP
- Japan
- Prior art keywords
- labeling reagent
- compound
- amino
- mass spectrometry
- reagent according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000002372 labelling Methods 0.000 claims description 39
- 239000003153 chemical reaction reagent Substances 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 238000004949 mass spectrometry Methods 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 8
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 7
- 150000001717 carbocyclic compounds Chemical group 0.000 claims description 6
- 238000004885 tandem mass spectrometry Methods 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 102000004169 proteins and genes Human genes 0.000 claims description 4
- 108090000623 proteins and genes Proteins 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 150000001413 amino acids Chemical class 0.000 claims description 2
- 238000005259 measurement Methods 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 238000002541 precursor ion scan Methods 0.000 claims description 2
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 2
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims description 2
- 238000002553 single reaction monitoring Methods 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- -1 carbamate compound Chemical class 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 125000005208 trialkylammonium group Chemical group 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001601 aromatic carbocyclic compounds Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000005412 pyrazyl group Chemical group 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002036446 | 2002-02-14 | ||
| JP2002036446 | 2002-02-14 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015188056A Division JP6278210B2 (ja) | 2002-02-14 | 2015-09-25 | アミノ官能性化合物の分析方法及び分析試薬 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020008872A Division JP7055267B2 (ja) | 2002-02-14 | 2020-01-23 | アミノ官能性化合物の分析方法及び分析試薬 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018052972A JP2018052972A (ja) | 2018-04-05 |
| JP2018052972A5 true JP2018052972A5 (enExample) | 2018-06-07 |
| JP6699645B2 JP6699645B2 (ja) | 2020-05-27 |
Family
ID=27678084
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003568398A Expired - Lifetime JP4453363B2 (ja) | 2002-02-14 | 2003-02-13 | アミノ官能性化合物の分析方法及び分析試薬 |
| JP2009269796A Expired - Lifetime JP5136542B2 (ja) | 2002-02-14 | 2009-11-27 | アミノ官能性化合物の分析方法及び分析試薬 |
| JP2012216013A Expired - Lifetime JP5842775B2 (ja) | 2002-02-14 | 2012-09-28 | アミノ官能性化合物の分析方法及び分析試薬 |
| JP2015188056A Expired - Lifetime JP6278210B2 (ja) | 2002-02-14 | 2015-09-25 | アミノ官能性化合物の分析方法及び分析試薬 |
| JP2017234081A Expired - Lifetime JP6699645B2 (ja) | 2002-02-14 | 2017-12-06 | アミノ官能性化合物の分析方法及び分析試薬 |
| JP2020008872A Expired - Lifetime JP7055267B2 (ja) | 2002-02-14 | 2020-01-23 | アミノ官能性化合物の分析方法及び分析試薬 |
Family Applications Before (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003568398A Expired - Lifetime JP4453363B2 (ja) | 2002-02-14 | 2003-02-13 | アミノ官能性化合物の分析方法及び分析試薬 |
| JP2009269796A Expired - Lifetime JP5136542B2 (ja) | 2002-02-14 | 2009-11-27 | アミノ官能性化合物の分析方法及び分析試薬 |
| JP2012216013A Expired - Lifetime JP5842775B2 (ja) | 2002-02-14 | 2012-09-28 | アミノ官能性化合物の分析方法及び分析試薬 |
| JP2015188056A Expired - Lifetime JP6278210B2 (ja) | 2002-02-14 | 2015-09-25 | アミノ官能性化合物の分析方法及び分析試薬 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020008872A Expired - Lifetime JP7055267B2 (ja) | 2002-02-14 | 2020-01-23 | アミノ官能性化合物の分析方法及び分析試薬 |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US7148069B2 (enExample) |
| EP (3) | EP2317307B1 (enExample) |
| JP (6) | JP4453363B2 (enExample) |
| AU (1) | AU2003211941A1 (enExample) |
| CA (1) | CA2475011C (enExample) |
| WO (1) | WO2003069328A1 (enExample) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2475011C (en) | 2002-02-14 | 2015-07-07 | Ajinomoto Co., Inc. | Method for analysis of compounds with amino group and analytical reagent therefor |
| US20050014279A1 (en) * | 2003-07-14 | 2005-01-20 | Nguyen Hoa Duc | Method of analysis of amine by mass spectrometry |
| US7759130B2 (en) * | 2003-11-21 | 2010-07-20 | Eisai R & D Management Co., Ltd. | Mass spectrometric quantitation method for biomolecules based on metabolically labeled internal standards |
| US20080206737A1 (en) * | 2004-05-19 | 2008-08-28 | Hunter Christie L | Expression quantification using mass spectrometry |
| US20070054345A1 (en) * | 2004-05-19 | 2007-03-08 | Hunter Christie L | Expression quantification using mass spectrometry |
| EP1750126B1 (en) | 2004-05-26 | 2015-09-16 | Ajinomoto Co., Inc. | Method and apparatus for analyzing aminofunctional compound |
| US20060172319A1 (en) * | 2004-07-12 | 2006-08-03 | Applera Corporation | Mass tags for quantitative analyses |
| US20070048752A1 (en) | 2004-07-12 | 2007-03-01 | Applera Corporation | Mass tags for quantitative analyses |
| US8969089B2 (en) | 2004-10-12 | 2015-03-03 | Quest Diagnostics Investments, Inc. | Analysis of amino acids in body fluid by liquid chromatography-mass spectrometry |
| US20060183238A1 (en) | 2005-02-09 | 2006-08-17 | Applera Corporation | Amine-containing compound analysis methods |
| JP2007163423A (ja) * | 2005-12-16 | 2007-06-28 | Ajinomoto Co Inc | 質量分析計によるアミノ酸分析方法 |
| US20110053196A1 (en) * | 2006-02-08 | 2011-03-03 | Nec Corporation | Method for modifying a peptide and a method for identifying a peptide |
| EP1983346A4 (en) * | 2006-02-08 | 2010-03-17 | Nec Corp | METHOD FOR CLEAVING A PEPTIDE BOND AT THE C-TERMINAL END OF A PEPTIDE, AND A METHOD FOR DETERMINING THE C-TERMINAL END-ACE AMINO ACID SEQUENCE OF A PEPTIDE |
| US12367163B2 (en) | 2007-06-29 | 2025-07-22 | Quest Diagnostics Investments Llc | Analysis of amino acids in body fluid by liquid chromatography—mass spectrometry |
| CA2691974C (en) * | 2007-06-29 | 2016-08-30 | Quest Diagnostics Investments Incorporated | Analysis of amino acids in body fluid by liquid chromatography-mass spectrometry |
| WO2009054350A1 (ja) | 2007-10-25 | 2009-04-30 | Ajinomoto Co., Inc. | 耐糖能異常の評価方法 |
| WO2009070233A1 (en) * | 2007-11-26 | 2009-06-04 | Waters Technologies Corporation | Internal standards and methods for use in quantitatively measuring analytes in a sample |
| EP2252584B1 (en) | 2008-02-04 | 2016-12-07 | Prozyme, Inc. | Compounds and methods for rapid labeling of n-glycans |
| DE102009060102A1 (de) * | 2009-12-21 | 2011-06-22 | Martin-Luther-Universität Halle-Wittenberg, 06108 | Derivatisierungsreagenzien zur tandem-massenspektrometrischen Quantifizierung von Proteinen |
| CN106226527B (zh) | 2011-07-21 | 2018-05-04 | 和光纯药工业株式会社 | 血浆中氨基酸分析用内标液、内标物质及血浆中氨基酸的定量方法 |
| US10436790B2 (en) | 2011-09-28 | 2019-10-08 | Waters Technologies Corporation | Rapid fluorescence tagging of glycans and other biomolecules with enhanced MS signals |
| US11352325B2 (en) | 2011-09-28 | 2022-06-07 | Waters Technologies Corporation | Rapid fluorescence tagging of glycans and other biomolecules with enhanced MS signals |
| WO2013049622A1 (en) | 2011-09-28 | 2013-04-04 | Waters Technologies Corporation | Rapid fluorescence tagging of glycans and other biomolecules with enhanced ms signals |
| WO2013078222A1 (en) | 2011-11-23 | 2013-05-30 | Quest Diagnostics Investments Incorporated | Kisspeptin-54 detection by tandem mass spectrometry |
| WO2014084290A1 (ja) | 2012-11-27 | 2014-06-05 | 味の素株式会社 | 膵臓癌の評価方法、膵臓癌評価装置、膵臓癌評価方法、膵臓癌評価プログラム、膵臓癌評価システムおよび情報通信端末装置 |
| EP3213056B1 (en) | 2014-10-30 | 2020-08-12 | Waters Technologies Corporation | Methods for the rapid preparation of labeled glycosylamines and for the analysis of glycosylated biomolecules producing the same |
| WO2016077548A1 (en) | 2014-11-13 | 2016-05-19 | Waters Technologies Corporation | Methods for liquid chromatography calibration for rapid labeled n-glycans |
| KR101627841B1 (ko) * | 2015-05-27 | 2016-06-07 | 다이아텍코리아 주식회사 | 싸이오크로멘 타입 화합물 및 그 용도 |
| HUE052637T2 (hu) | 2015-05-29 | 2021-05-28 | Agilent Technologies Inc | Olyan vegyületek melyek amin-tartalmú vegyületek jelölésére szolgálnak és ezeknek a felhasználásuk |
| CN105548432A (zh) * | 2015-12-18 | 2016-05-04 | 乐普药业股份有限公司 | 一种比伐卢定中氨基酸的检测分析方法 |
| US12252557B2 (en) | 2016-04-24 | 2025-03-18 | Waters Technologies Corporation | Charged surface reversed phase chromatographic materials method for analysis of glycans modified with amphipathic, strongly basic moieties |
| US11035832B2 (en) | 2016-06-21 | 2021-06-15 | Waters Technologies Corporation | Methods of electrospray ionization of glycans modified with amphipathic, strongly basic moieties |
| EP3472132A4 (en) | 2016-06-21 | 2020-01-15 | Waters Technologies Corporation | FLUORESCENCE LABELING OF GLYCANS AND OTHER BIOMOLECULES BY REDUCING AMINATION FOR IMPROVED MASS SPECTROMETRY SIGNALS |
| CN109313203B (zh) | 2016-06-30 | 2023-01-06 | 味之素株式会社 | 分娩后酮病的评价方法 |
| EP3479103B1 (en) | 2016-07-01 | 2022-04-20 | Waters Technologies Corporation | Methods for the rapid preparation of labeled glycosylamines from complex matrices using molecular weight cut off filtration and on-filter deglycosylation |
| US20180094293A1 (en) | 2016-10-03 | 2018-04-05 | Waters Technologies Corporation | Labeled glycan amino acid complexes useful in lc-ms analysis and methods of making the same |
| EP3692372B1 (en) * | 2017-09-08 | 2024-04-17 | F. Hoffmann-La Roche AG | Sulfoxide-based reagent for mass spectrometry |
| EP3732959A4 (en) | 2017-12-28 | 2022-03-30 | Ajinomoto Co., Inc. | POWER CONTROL SYSTEM AND METHOD OF POWER CONTROL |
| EP3859339A4 (en) | 2018-09-26 | 2022-12-28 | Ajinomoto Co., Inc. | METHOD FOR ASSESSING MILD COGNITIVE IMPAIRMENTS, CALCULATION METHOD, ASSESSMENT DEVICE, CALCULATION DEVICE, ASSESSMENT PROGRAM, CALCULATION PROGRAM, RECORDING MEDIA, ASSESSMENT SYSTEM AND TERMINAL |
| CN116773710A (zh) * | 2021-07-13 | 2023-09-19 | 清华大学 | 一种覆盖多种代谢物的代谢组和代谢流的试剂盒和使用方法 |
| CN114354801B (zh) * | 2021-12-31 | 2023-07-18 | 山东大学 | （R）-3-Boc-氨基哌啶中三种氨基吡啶异构体含量的分析方法 |
| CN115925614B (zh) * | 2022-12-02 | 2024-03-08 | 中山大学 | 用于发现可与醛基反应的活性物质的小分子探针 |
| JPWO2024225424A1 (enExample) | 2023-04-28 | 2024-10-31 |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4003912A (en) * | 1973-06-11 | 1977-01-18 | Monsanto Company | Dicarboximido-N-phenylsubstituted carbamates and derivatives |
| JPS5855754A (ja) | 1981-09-30 | 1983-04-02 | Hitachi Ltd | アミノ酸分析方法 |
| JPS6444848A (en) | 1987-08-14 | 1989-02-17 | Hitachi Ltd | Analysis of amino acid |
| US5296599A (en) * | 1991-09-19 | 1994-03-22 | Millipore Corporation | Activated carbamates compounds |
| EP0804735A4 (en) * | 1994-07-08 | 1999-12-22 | Hope City | N-TERMINAL PROTEIN SEQUENCING REAGENTS AND METHODS THAT MAKE AMINO ACID DERIVATIVES |
| JP3346965B2 (ja) * | 1995-09-14 | 2002-11-18 | 株式会社日立製作所 | アミノ酸分析装置 |
| TW358097B (en) * | 1996-05-24 | 1999-05-11 | Hoffmann La Roche | Beta-lactams and their process and pharmaceutical compositions |
| JP4085443B2 (ja) | 1997-05-07 | 2008-05-14 | 株式会社島津製作所 | アミノ酸の分析試薬及びアミノ酸の分析方法 |
| US6379971B1 (en) * | 1998-02-24 | 2002-04-30 | Target Discovery, Inc. | Methods for sequencing proteins |
| ATE253126T1 (de) * | 1998-08-25 | 2003-11-15 | Univ Washington | Schnelle quantitative analyse von proteinen oder proteinfunktionen in komplexen gemischen |
| GB9821393D0 (en) | 1998-10-01 | 1998-11-25 | Brax Genomics Ltd | Protein profiling 2 |
| US6629040B1 (en) * | 1999-03-19 | 2003-09-30 | University Of Washington | Isotope distribution encoded tags for protein identification |
| US6677114B1 (en) * | 1999-04-20 | 2004-01-13 | Target Discovery, Inc. | Polypeptide fingerprinting methods and bioinformatics database system |
| JP4505905B2 (ja) | 1999-11-22 | 2010-07-21 | 住友化学株式会社 | ペプチドのアミノ酸配列決定方法 |
| JP3341041B2 (ja) * | 2000-02-23 | 2002-11-05 | 独立行政法人産業技術総合研究所 | ペプチドのアミノ酸配列解析方法 |
| AUPQ664300A0 (en) * | 2000-04-03 | 2000-05-04 | Proteome Systems Ltd | Macromolecule detection |
| US6716634B1 (en) * | 2000-05-31 | 2004-04-06 | Agilent Technologies, Inc. | Increasing ionization efficiency in mass spectrometry |
| WO2002004936A1 (fr) * | 2000-07-11 | 2002-01-17 | Japan Science And Technology Corporation | Sonde pour spectrometrie de masse d'un echantillon liquide |
| US20060141632A1 (en) * | 2000-07-25 | 2006-06-29 | The Procter & Gamble Co. | New methods and kits for sequencing polypeptides |
| JP3508710B2 (ja) * | 2000-09-01 | 2004-03-22 | 株式会社日立製作所 | アミノ酸分析方法および装置 |
| WO2002048717A2 (en) * | 2000-10-23 | 2002-06-20 | Genetics Institute, Llc. | Acid-labile isotope-coded extractant (alice) in mass spectrometric analysis |
| US6905879B2 (en) * | 2000-10-23 | 2005-06-14 | Genetics Institute, Inc. | Isotope-coded ionization-enhancing reagents (ICIER) for high-throughput protein identification and quantitation using matrix-assisted laser desorption ionization mass spectrometry |
| US20030045552A1 (en) * | 2000-12-27 | 2003-03-06 | Robarge Michael J. | Isoindole-imide compounds, compositions, and uses thereof |
| US6818454B2 (en) * | 2001-02-16 | 2004-11-16 | Battelle Memorial Institute | Phosphoprotein binding agents and methods of their use |
| JP3464665B2 (ja) | 2002-01-07 | 2003-11-10 | 株式会社日立製作所 | アミノ酸分析装置 |
| CA2475011C (en) * | 2002-02-14 | 2015-07-07 | Ajinomoto Co., Inc. | Method for analysis of compounds with amino group and analytical reagent therefor |
| EP1750126B1 (en) * | 2004-05-26 | 2015-09-16 | Ajinomoto Co., Inc. | Method and apparatus for analyzing aminofunctional compound |
-
2003
- 2003-02-13 CA CA2475011A patent/CA2475011C/en not_active Expired - Lifetime
- 2003-02-13 EP EP10012963.4A patent/EP2317307B1/en not_active Expired - Lifetime
- 2003-02-13 JP JP2003568398A patent/JP4453363B2/ja not_active Expired - Lifetime
- 2003-02-13 WO PCT/JP2003/001463 patent/WO2003069328A1/ja not_active Ceased
- 2003-02-13 AU AU2003211941A patent/AU2003211941A1/en not_active Abandoned
- 2003-02-13 EP EP03705088.7A patent/EP1475632B1/en not_active Expired - Lifetime
- 2003-02-13 EP EP10012964A patent/EP2336763A1/en not_active Withdrawn
-
2004
- 2004-08-16 US US10/918,380 patent/US7148069B2/en not_active Expired - Lifetime
-
2006
- 2006-09-01 US US11/514,130 patent/US9274123B2/en not_active Expired - Fee Related
-
2009
- 2009-11-27 JP JP2009269796A patent/JP5136542B2/ja not_active Expired - Lifetime
-
2012
- 2012-09-28 JP JP2012216013A patent/JP5842775B2/ja not_active Expired - Lifetime
-
2015
- 2015-09-25 JP JP2015188056A patent/JP6278210B2/ja not_active Expired - Lifetime
-
2016
- 2016-01-21 US US15/003,235 patent/US9658234B2/en not_active Expired - Lifetime
-
2017
- 2017-12-06 JP JP2017234081A patent/JP6699645B2/ja not_active Expired - Lifetime
-
2020
- 2020-01-23 JP JP2020008872A patent/JP7055267B2/ja not_active Expired - Lifetime
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2018052972A5 (enExample) | ||
| JP2013015537A5 (enExample) | ||
| JP7055267B2 (ja) | アミノ官能性化合物の分析方法及び分析試薬 | |
| CN105102682B (zh) | 苯胺类化合物的电化学偶合 | |
| JP2010071995A5 (enExample) | ||
| Brotzel et al. | Nucleophilicities of primary and secondary amines in water | |
| Bouchoux | Gas phase basicities of polyfunctional molecules. Part 3: Amino acids | |
| US20040142378A1 (en) | Probe for mass spectrometry of liquid sample | |
| US10336713B2 (en) | Triazole-based reader molecules and methods for synthesizing and use thereof | |
| Chen et al. | Iodine mediated deprotection of N-tert-butanesulfinyl amines: a functional group compatible method | |
| JP2015524058A5 (enExample) | ||
| JP2018538511A (ja) | 高スループット定量的プロテオミクス及びペプチドミクスのための質量欠損ベースの多重化ジメチルピリミジニルオルニチン（ｄｉｐｙｒｏ）タグ | |
| JP2018538511A5 (enExample) | ||
| Seybold | Quantum Chemical‐QSPR Estimation of the Acidities and Basicities of Organic Compounds | |
| Solís-Calero et al. | DFT study of the mechanism of the reaction of aminoguanidine with methylglyoxal | |
| Elrod | A comprehensive computational investigation of the enthalpies of formation and proton affinities of C4H7N and C3H3ON compounds | |
| RU2005131004A (ru) | Способ оределения молекулярной массы соединения, содержащего моноэфир фосфорной кислоты, и добавка для масс-спектрометрии | |
| Gilman et al. | The Identification of Organomagnesium Halides by Crystalline Derivatives Prepared from α-Naphthyl Isocyanate | |
| JP2013523646A5 (enExample) | ||
| CN114105858A (zh) | 3-叠氮二氢吲哚类化合物及电化学合成3-叠氮二氢吲哚类化合物的方法 | |
| Muetterties et al. | Gas-phase acid-base properties of 1-aminocycloalkane-1-carboxylic acids from the extended kinetic method | |
| TN2018000168A1 (fr) | Procédés d'extraction et de récupération de l'uranium présent dans une solution aqueuse comprenant de l'acide phosphorique | |
| JP2007070293A (ja) | イオン性液体合成方法及びイオン性液体 | |
| RU2560180C1 (ru) | N'-(1-метилэтилиден)гептадекафтороктилкарбоксамидразон в качестве стандартного образца состава для количественного определения фтора в органических соединениях спектрофотометрическим методом, способ его получения и промежуточное соединение | |
| JP2006526645A5 (enExample) |